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. 2018 Oct 8;16(10):371.
doi: 10.3390/md16100371.

New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Francisco Javier Ortiz-López  1 , Elsa Alcalde  2 , Aida Sarmiento-Vizcaíno  3 , Caridad Díaz  4 , Bastien Cautain  5 , Luis A García  6 , Gloria Blanco  7 , Fernando Reyes  8
Affiliations

New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Francisco Javier Ortiz-López et al. Mar Drugs. .

Abstract

Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1⁻3) containing different amino acid residues. The structures of the new molecules (1⁻3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey's analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1⁻3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC50 values of 15.6 and 51.5 µM for compounds 5 and 1, respectively.

Keywords: 3-hydroxyquinaldic acid; Cantabrian Sea; Streptomyces cyaneofuscatus; deep-sea actinobacteria.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Neighbour-joining phylogenetic tree obtained by distance matrix analysis of 16S rDNA sequences, showing Streptomyces cyaneofuscatus M-157 position and most closely related phylogenetic neighbours. Numbers on branch nodes are bootstrap values (1000 resamplings; only values >50% are given). Asterisks indicate that the corresponding nodes were also recovered in the maximum likelihood tree. Bar indicates 0.1% sequence divergence.
Figure 2
Figure 2
Compounds isolated from Streptomyces cyaneofuscatus M-157.
Figure 3
Figure 3
COSY and HMBC correlations observed in the structure of 1.
Figure 4
Figure 4
COSY and HMBC correlations observed in the structure of 2.
Figure 5
Figure 5
COSY and HMBC correlations observed in the structure of 6.
See this image and copyright information in PMC

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